One Month Ago I Left My Job for a Startup

Everyone tells you to find your passion. That doing what you love leads to self-fulfillment and happiness in your career. Well, the reverse is also true. After I sold my first company last year, I agreed to an employment contract as a condition of the sale. The allure of a paycheck, corporate things (Health Insurance! 401k! Synergies!), and a break from the startup grind seemed magical at the time.

Fast forward a year later, I was broken — chronically depressed, thirty pounds heavier with weight gain spiraling out of control, and a spark in me that was all but dead. Worst of all was how my personal relationships suffered. I missed what would be the last Thanksgiving with my father. He passed away in December. My new marriage was heading off a cliff. All the while, I had to plaster on a fake smile and pretend that this was normal. That this was ok. And it wasn’t. I wasn’t. Something had to change.

I recall venting to someone who straight up asked me if I was so miserable, why was I still there? And I really didn’t have a good answer. Just excuses. Sometimes we are our own biggest barriers to happiness. Fear drives us to make decisions that ultimately hold us back. The fear of not having a paycheck. The fear of walking out on the company I spent the last half decade of my life building. The fear of the unknown. And while many of these were not entirely irrational, the opportunity cost of not pursuing my next big thing was weighing on me, my family, and job performance. I had hit a wall. So finally at the end of May, I got out. It was a mutual separation that was in everyone’s best interest.

Ironically, the best sleep I’d had in three years was the day I left my job. The very next morning I was on a flight to visit potential client sites. And I haven’t stopped since. Over the last few weeks I’ve been to 92 stores to validate our assumptions and build a solution that truly solves our customer’s most pressing challenges, secured commitments to bring our product into 1000’s of locations, and rebuilt a team from zero to four. I’ve loved every moment of it. It’s amazing what you can accomplish when you are challenged to be laser focused and go all in on your own.

I am an entrepreneur. I love solving, building, and leaving my mark on the world. There’s nothing more fulfilling to me than working with talented people and incredible clients who challenge me every day to push the limits on what we thought was possible. As entrepreneurs, we seek to control our own destiny. And while you can’t control life, I believe we have everything we need to navigate through it.

I’ll continue to share my personal thoughts, ideas, and stories from the frontline as we continue in our journey to grow RetailAware.

To be continued…